


How Dean Winchester Systematically Fucked Himself Over

by haikuhamster



Category: Supernatural
Genre: Anal Sex, Bottom Dean, Bottom Jimmy (Implied), Cockslut Dean, Dirty Talk, Jock Straps, M/M, Multi, Rough Sex, Size Queen Dean, Sub Dean, Top Castiel, Top Jimmy, Truth or Dare, Twincest (implied), angsty communist threesome, exhibitionism (implied)
Language: English
Status: Completed
Published: 2018-03-20
Updated: 2018-03-20
Packaged: 2019-04-05 00:13:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,434
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14031936
Author URL: https://archiveofourown.org/users/haikuhamster/pseuds/haikuhamster
Summary: A typical truth or dare game! Hooray, college! Until Dean tries to win. That was a mistake....Still turned out great.





	How Dean Winchester Systematically Fucked Himself Over

**Author's Note:**

> Hoooooooly shit. Wowie. This is, uh... something. Even writing this I was like, “THIS IS A SIN. THIS IS DEFINITELY A SIN. I’M AN ATHEIST BUT I STILL THINK I MAY GO TO ATHEIST HELL FOR THIS.”
> 
> I took the college truth or dare idea and tried to make the ending a little different than usual and I think I did alright there? Sure hope so.

“What teacher would you most like to fuck, if given the chance?”

“Oh, that’s not even a question,” Dean said. “Ms. Jones. God, have you even fucking seen her?”

“She could punch me in the face and I’d thank her.”

“...Maybe you should lay off the Jack for a bit, Benny.”

All four of the guys laughed at that, including Jimmy, who made the joke in the first place. Benny was the only one who’d drank so far, everyone else having done everything asked in the game.

Truth or dare was essentially a college staple, right? Benny was roommates with Jimmy, who introduced him to Castiel, being his brother. Dean was roommates with Castiel, and was thus dragged into all of this. Not that he minded.

The guys were fucking great. Castiel was a bit of an ass at first, but that was just because Dean didn’t understand his dry wit. He’d met Jimmy, the eccentric twin, and suddenly it was like the last piece had been added to the puzzle. Castiel wasn’t a snide dick, he was intelligent and sweet. 

The twins were incredible, though Dean would never tell them that to their faces.

“Speaking of Benny, truth or dare?” Dean asked. 

“Dare,” the man challenged with a shit-eating grin.

“Ideas?” Dean asked. Jimmy quickly waved him over and whispered into his ear, before they both pulled away and snorted out laughter. “Alright, Benny, through a thought that was completely my own, I dare you to go outside and sing All Star by Smash Mouth. Loudly. In your underwear.”

Benny looked at Dean and Jimmy, horrified, and they both laughed. “Hell no,” he said, reaching for the alcohol. “You couldn’t pay me to do that.”

Castiel grabbed the bottle of Jack Daniel’s before Benny could, and raised an eyebrow at him. “You don’t get to drink our liquor and not play the game.”

“Yeah Benny, nut up or get out,” Jimmy insisted. The man in question rolled his eyes and got up to leave. If they didn’t know him better, they would’ve asked him to stay, but Benny was probably waiting until the moment they gave him an excuse to leave anyway. He worked way too much.

When the door was shut, Castiel placed the whiskey back on the table. “Alright, Dean. We won’t count the last one, so just go again.”

“Alright, uh... Cas. Truth or dare?”

“Truth.”

“How many girls have you kissed?”

Jimmy smirked, and Castiel hit him in the arm. “None.”

“Really? You’ve never had your first kiss?”

“I wouldn’t-“ Jimmy started, but Castiel quickly hit him again. They made eye contact for a moment, after which Jimmy schooled his face. “Sorry.”

Castiel smirked, probably a little cocky about shutting his little brother up with a look. Dean knew the feeling and suppressed a smile too. “Alright, Jimmy, truth or dare?”

“Truth,” the twin replied, warily.

Castiel grinned wickedly. “How many girls have _you_ kissed?”

Jimmy looked at him petulantly. “You know the answer.”

“He doesn’t,” Castiel argued, gesturing to Dean. “Share with us your escapades, brother. Tell Dean about all the girls you get.”

“Zilch,” Jimmy snapped, and Castiel sat back, his lips pulled into a satisfied smile. Jimmy rolled his eyes, but turned to Dean without complaining any more. “Truth or dare?”

“Dare, I guess.”

“Give me a lap dance,” Jimmy ordered. The shit-eating was right back on his face. “60 seconds. No funny business though, I’m waiting ‘til marriage.”

Dean’s initial embarrassment was eased by the joke at the end. “Don’t wanna interrupt your streak of not getting laid.” He climbed onto Jimmy’s lap, awkwardly grinding down and up. He didn’t even make eye contact with him. God, the whole thing felt so weird.

“No touching the dancers, Jimmy,” Castiel said around the 20th second. “You know the rules.”

Dean kept wiggling around in hopes of recreating those sexy movie scenes, but he knew he was failing miserably. Jimmy agreed, clearly, because he argued to Cas, “I’m gonna guide his hips. Look at him, he’s lost!”

Dean’s mortification came back with a vengeance, and he lost count of the seconds in his head. He buried his face in the couch behind Jimmy’s shoulder and groaned in agony, stopping his movements.

“Look what you did, brother,” Castiel scolded. “Now how am I going to get a lap dance too?”

Dean laughed a little hysterically into the pillow, still not bothering to get off Jimmy or raise his head. If he didn’t acknowledge it, he could pretend the situation wasn’t really happening. 

“Pay him with better liquor, for one,” Jimmy suggested. “And let me teach him how to do it so he’s more confident.”

“Grabbing someone without their consent is not how education works, even in the fucked-up American system,” Castiel argued. “Dean, you may sit back down. Your dare is completed.”

Dean sprang up, stumbling back to his chair. He desperately wanted to down a shot, if only to distract himself from the feeling of his cheeks flaming. “Jimmy, truth or dare,” he muttered.

“Dare.”

He told his mind to ask _show us what color your underwear is_ , but his mouth decided to say, “show me how to give a lap dance”. His eyes bulged at his own verbal barfing, but Jimmy threw his head back and laughed.

“Hell yeah.” Suddenly, Dean’s lap was full of Jimmy, who was wiggling his eyebrows. He started to grind a bit, making Dean’s head spin. He lifted up and rose down and Dean felt like he was losing his mind, because How was this his fucking life right now? His body was frozen under Jimmy...

Until he stopped out of nowhere. Dean could see the mischief enter his eyes before he opened his mouth. “Actually...” he jumped off of Dean. “You’ll learn better watching from a distance. Pay close attention to my hips, Dean. I’ll be slow.”

With that, he jumped into Cas’ lap and— holy shit. Whereas with Dean he was mostly just moving his hips to an imaginary beat, he’s full-on emulating sex here. Dean flashed his eyes up to Castiel’s and found him glaring intensely at his brother. His face remained stoic but his eyes held a controlled rage Dean had never seen on him. 

It’s so fucking hot Dean almost wanted to cry.

He was no stranger to his own... preferences. He didn’t talk about it, never came out, and definitely had never acted on it. He just kinda liked porn that distributed its focus between both the girl and the guy. No biggie.

Dean focused again, and barely held back a groan. True to his word, Jimmy was slow, and thorough. He didn’t lift his hips up, just ground his cock straight into his brother’s, and when he pulled back, it was his ass on Castiel’s cock instead. Dean was a little horrified at himself for wishing he could watch his friends— this pair of _twin brothers_ — fuck. Jimmy had an incredible ass, and from the glances Dean had got of Castiel’s morning wood (who slept naked in a shared room?), the older twin was definitely above average.

Jimmy climbed off abruptly, smirking over at Dean as if he’d read his mind. Dean schooled his face to look completely stoic, though he knew his cheeks were pink. Castiel was breathing deeply, as though willing away the anger. Dean was sickened at his own mind, seeing how uncomfortable Cas was. Dean had been wishing it had gone farther, but Castiel had hated it.

Jimmy’s voice broke Dean out of his own head. “Truth or dare, Castiel?”

Castiel’s voice was apathetic when he replied once again, “truth.”

“Are you a virgin?”

Dean cocked his head to the side. That was a weird question. “He’s never even kissed a girl, why would he have-“

Castiel cut him off with the terse answer, “No.”

Dean gaped for a minute, while Jimmy giggled into his own hand. “You slept with someone and you didn’t even kiss her?”

Jimmy threw his head back at that, and even Castiel broke into a grin. They looked at each other knowingly, before Jimmy turned back to Dean. “You think I’d let my brother go into college a virgin?”

Dean looked between them again, totally lost. There was something here he didn’t know, and it was frustrating him. Castiel interrupted his monologue with the question, though. “Truth or dare, Dean?”

Dean squinted at them, feeling the tension in the room as this became a game he was suddenly losing. How could he bring it back when he didn’t know what he was even doing wrong? “Uh... dare, I guess.”

“Give Jimmy a hickey.”

Dean spluttered indignantly, choking on air. He coughed for a bit, then caught his breath. “What?” he asked, his voice raspy.

“I think the instructions were rather clear, Dean. Unless you’re chicken?” Jimmy said with a smug grin. Dean wanted to crawl into a hole for a long time.

Castiel, ever vigilant, sensed Dean’s discomfort. “How about this, instead?” Jimmy’s head snapped towards him, his features looking miffed at the idea that he might not be getting a hickey from his brother’s roommate. “Either you give him two hickeys, or you take 3 shots and remove your shirt for the rest of the game.”

“Why two hickeys?” Dean asked. 

“Because it makes your choices a little more equal in discomfort,” Castiel said. He was right. Fuck. “Which is it? My brother or your shirt?”

Dean looked at Jimmy, who gave him a little nod. Dean caught the meaning, that either way was completely acceptable so long as it made him more comfortable. “I uh, I’m gonna go for the shots... I don’t think I could handle a week of seeing my own hickeys on a carbon-copy of my roommate.” He laughed nervously, biting his lip when neither twin laughed with him.

He leaned over to grab the Jack and his glass, until Castiel batted his hand away. “Shirt first.”

Dean looked him in the eyes for a moment, searching for something and not knowing what. He steeled himself and pulled his shirt off without ceremony, immediately going back to pour his first shot. He knocked the first one back, grateful for the distracting burn. The second followed shortly, then the third. It would take a second to kick in, but he was endlessly thankful to Cas for suggesting it over the former.

“Alrighty, then,” he said, once he was settled in his chair. He looked up to two pairs of blue eyes roving over his body. Castiel’s eyes were a bit slower, taking in everything, and Jimmy looked... hungry. Dean was a goner. “Uh, Jimmy. Truth or dare.”

“Truth,” he said, eyes snapping up to meet Dean’s. He winked, and Dean was at the end of his rope. Time to win.

“Who did Cas sleep with?” Both of the twins’ eyes snapped open wide, and they quickly looked at each other.

Jimmy silently leaned over to open the bottle of Jack and pour himself a shot. He downed it, then looked back at Dean. “Different question.”

Dean smirked at his little victory. “Have _you_ slept with anyone?”

Jimmy looked wary this time, instead of the usual mischief he displayed when talking about sex. “Yeah.”

Dean’s jaw dropped in disbelief. “Seriously? Neither of you even kissed the girls you banged?”

“That wasn’t part of the question, Dean,” Castiel said. Dean rolled his eyes.

“Truth or dare, brother?” Jimmy asked.

“Dare,” Cas said. Finally, the man broke his truth streak.

“I dare you to take your shirt off too,” Jimmy said. When Castiel looked at him in shock, he just argued, “It’s only fair. Dean’s gotta be getting lonely over there.”

Castiel looked at Dean again, then nodded. He slid his shirt off without circumstance. Dean already knew what his body looked like, having admittedly stared at his chest and arms one too many times while they changed in the mornings and nights. What surprised him was the marring of his skin.

Castiel had dark bruises scattered across his chest, and a bite mark on his left hip. Dean could see five marks on each bicep, like someone had dug their fingers in far too hard. His entire body looked fucking wrecked. Dean knew Castiel didn’t have a fuck buddy; the only people he ever hung out with were his brother, Benny, and Dean. Three dudes, and Castiel was straight.

“Christ almighty, dude,” Dean said, laughing to brush off the hunt of jealousy.

Castiel smiled and asked him, “Truth or dare, Dean?”

“Truth,” was the easy response.

“What’s your biggest kink?”

Dean gaped for a moment before closing his mouth finally. He thought about it for a moment, considering the pros and cons of even answering the question in the first place. Fuck it. “Exhibition.”

“Why?” Castiel asked.

“That wasn’t part of the question, Cas,” Dean parroted with a little smile. “Anyways, Jimmy. Truth or dare?”

“Truth.” Fucker. Dean only had dates in mind.

He had to go with a pretty standard question. “What do you usually jack off to?”

Jimmy grinned. “I don’t jack off.”

Dean scoffed. “Yeah, you do, idiot. Everybody does. Just answer the question.”

Jimmy looked at his brother, who shrugged. He looked back to Dean and cocked his head to the side. “Why, Dean, the same thing I always think about! The thought of my dingaling in a nice ol’ vajimjam, warm and cozy, until we have some nice, wholesome orgasms.”

Castiel outright laughed at that, head thrown back and a hand thrown over his chest. Dean couldn’t help but laugh too, even though he was a little disappointed at not getting a legit answer.

“I’ll let that slide because you made me laugh, you ass,” Dean chuckled.

“You are what you eat,” Jimmy said with a wink. “Back to you, Dean, truth or dare?”

“Dare.”

“I dare you to take your pants off.”

Dean’s eyes widened, and he looked between the two twins. He found two blank faces staring at him, as he always did when he was looking for some actual answers to the million questions running through his head. He steeled himself anyway, standing up.

On second thought... fuck it. This was a game. They were playing a game, and goddammit if Dean Winchester was going to lose truth or dare to two twins in his own dorm. Hell no. He turned around, unbuttoned his jeans, and unzipped them slowly. Deliberately. The teeth of the zipper were deafening in the quiet of the room.

He inched his pants down slowly, bending over as he went. He knew the kind of view the twins were getting, how awesome his ass looked in his jockstrap. It was confirmed by the two gasps he heard behind him, and one tiny groan from Jimmy. He stepped out of the pants on light feet, kicking them away when he was done.

Dean sat back down as though nothing happened. “Alright, Cas, truth or dare?”

The man was flushed all down his chest, the blush matting across the tan skin. God, Cas was hot. Dean could feel himself getting hard, but what. He could ignore it... Probably.

“T-truth,” Castiel stuttered.

“If you would go gay for anyone, who would it be?” Dean asked.

“My brother,” he deadpanned. Dean and Jimmy both laughed, albeit Jimmy a little stilted. Castiel didn’t take his eyes off of dean when he addressed his brother. “Jimmy, truth or dare?”

“Truth.”

“Would you fuck Dean if he asked you to?” Dean felt his cock twitch and his eyes widen. Oh fuck.

“That’s not even a question,” Jimmy said, gaze traveling up Deans body before landing on his eyes. “But I’d prefer if he begged me to.”

Dean heard himself whimper and felt goosebumps rise up from under his skin. Fuck. They had to be messing with him. “Truth or dare, Castiel?”

“Dare.”

“I dare you to take your pants off too.”

Oh god. Oh god, that’s not something someone dares their brother to do. Dean could never see himself daring Sammy to do that. Unless he was in front of Jess and wearing Spider-Man boxers or something dumb like that. Was Cas wearing something stupid?

Castiel stood up, smirking as he shoved his pants down to his ankles. Dean only had a moment to be confused until he realized that- holy hell- Castiel was not wearing underwear. Oh god. Oh god. Ohhhhh god.

Castiel was half-hard, and fuck Dean should probably not have been staring for so long but he couldn’t avert his eyes if he tried. Castiel had sat back down next to his brother, totally naked, cock slowly growing against his hip where it lay.

“Dean, truth or dare?” Castiel asked.

Dean’s eyes snapped up, guilt fluttering through his stomach like butterflies. “Uh... truth.”

“Do you want to suck my cock, Dean?” God, his voice... Dean didn’t realize he was nodding desperately until he heard Jimmy chuckle. “Good. Take your turn, Dean.”

Oh fuck. Dean wanted Jimmy to leave so he could work on trying to make Castiel go gay. “Jimmy, truth or dare?”

“Truth.”

Dean’s mouth ran on autopilot. “Are you wearing underwear?”

“Never. Truth or dare, Dean?”

“Dare.”

“Give Castiel a blowjob.”

Dean whined, jumping out of his chair and onto his knees before he could even consider the oddity of the request. God, these guys were brothers. Fuck, Jimmy had just asked Dean to suck off his brother, his _twin_. Dean should’ve felt worse about it than he did.

He immediately dove in the second he was close enough, grabbing Castiel’s cock and lowering his mouth on it. He moaned at the taste, so wonderfully masculine. He tried to take it all the way into his mouth, but it choked him three fourths of the way down. Fuck, that was hot. He hadn’t choked on a cock since the first one he ever sucked.

He couldn’t bother doing tricks, though he wanted to make it good. This wasn’t even so much for Cas’ enjoyment as it was his own. Dean was having the time of his fucking life. He moved quickly, up and down, slurping messily and using his hand to jack off what he couldn’t get in his throat.

“Is he good, Cas?” Jimmy said, and Dean felt a hand in his hair.

“So fucking good,” Castiel groaned. “Fuck, he feels so good. He’s so perfect, Jimmy.” Dean drew his eyes up right in time to see Castiel dig a hand in Jimmy’s hair and pull his twin in for a kiss.

Holy fuck. Oh god. Dean was about to fucking come and he hadn’t even come close to touching himself. He could see Castiel’s tongue intertwining with Jimmy’s, both of them moaning into it. The sight, the sound...

Dean shot a hand down to grip his cock, stopping himself from coming on the spot. “I- ngh...” he whined, pitifully.

He watched the trail of spit connect their mouths as the boys pulled away, twin blue eyes looking down at him. Jimmy cooed at him. “Do you wanna come, Dean?” He nodded desperately against Castiel’s thigh. “Make yourself come, baby.”

He shook his head, a wrecked little sob bubbling in his chest. “Aw, little one,” Castiel soothed. “It looks like our baby is a little sub, huh? Do you want us to make you come instead?”

Dean nodded again, then laved wet kisses up Castiel’s cock. He watched as Cas threw his head back and groaned, and Jimmy’s hand started stroking his hair.

“Come up here and kiss me, Dean. Cas is gonna make you come,” Jimmy said. God, those words were perfect. Dean felt himself drifting through subspace, and knew he probably had been since Castiel took his pants off. Oh well. He trusted the twins. God, he trusted them. They were gonna make him come a ton and he was gonna be so good for them, always he was always a good boy he could be so good—

Jimmy’s lips were soft on Dean’s, and the feeling was almost odd. He didn’t remember climbing up onto the couch with him, sitting in his lip. He felt Jimmy’s hands land on his hips, holding him softly and rubbing his thumbs against Dean’s skin. A hand gently slapped his ass. Castiel groaned at the sight, and hit him again.

Dean moaned into Jimmy’s mouth and arched his back a bit, sticking his ass out in invitation. He didn’t care what happened. He had Cas behind him gawking at his best feature, and Jimmy in front of him sucking the taste of Castiel’s cock straight off his tongue. Fuck, this was perfect.

“Spread his cheeks open for me, Jimmy,” Castiel demanded. Jimmy obliged though, not before laying down a volley of three sharp slaps that had Dean gasping and burying his head in Jimmy’s shoulder. “God, Dean, you’re... gorgeous.”

Castiel must've been a boy scout in another life, because there’s no way he could’ve popped lube out of the sky otherwise. Yet, his finger was wet where it prodded at Dean’s hole. He slowly eased it in, and out, and in more, and out, until his entire finger was buried inside of Dean.

He didn’t touch Dean’s prostate, likely on purpose, because he didn’t seem to be searching for it either. When Dean’s muscles relaxed around the digit, he added another. The stretch was minuscule, but he still went slow and careful, so sweet with it. When he entered a third finger, Dean realized he was rutting against Jimmy’s shirt. Fuck, Jimmy was still clothed.

He desperately tugged at Jimmy’s shirt, whining when he couldn’t make much headway without messing with the steady rhythm of Castiel’s fingers in him. Jimmy chuckled and leaned back, letting go of Dean’s ass to pull his shirt off and shuffle his pants down and off. When he was naked, Castiel pulled his fingers out of Dean.

Dean looked at Cas, a pout on his lips. The man just smiled softly at him. “Jimmy is going to fuck you, and I will fuck you after him.”

Dean protested harder. “Both?”

Both the twins laughed. “Next time, little one,” Jimmy promised. “We don’t have the patience to stretch you this time.”

Dean nodded, still feeling disappointed. He could reconcile it to himself that they wanted him way too bad to wait until he was prepped. Given how big Cas was, Dean would be torn apart if he didn’t take the time to ease into two of him.

“You ready?” Jimmy asked, and Dean felt his cock tap against his entrance.

“Please, Jimmy,” he begged. “Fuck me, please, I need you to fuck me, please— _ohhhh fuck..._ ”

Jimmy eased him down slowly, but the stretch still burned. It was absolutely delicious. When he was all the way down, he could practically feel it in his stomach. Fuck, it was so good, so fucking good.

Dean lifted himself up after a moment, feeling his muscles protest as Jimmy exited his body inch by inch. He slammed back down soon enough, and Jimmy’s groan was breathtaking. He repeated the action, building a rhythm.

When Jimmy started thrusting up into him, Dean knew he was a goner. He had been close to coming with no stimulation earlier, but now with his prostate being slammed into? Fuck, he was gonna—

Dean clenched and shook and moaned his way through his orgasm, feeling his own cum pump out into his jockstrap. He felt Jimmy’s hips stuttering beneath him, riding out his own orgasm. He kept grinding down, desperate to milk Jimmy, to make himself sloppy for Cas. God, he wanted to be their little slut.

Jimmy eventually pulled him off, oversensitive. Dean, still wobbly and jelly-legged, hopped off of him and right into Cas’ lap. He didn’t hesitate, lining himself up and slamming down.

He’d been riding Cas for all of ten seconds before he was yanked off, his head slammed into Jimmy’s lap and his ass pulled up into the air. Castiel entered him again, slamming into him ruthlessly and starting a brutal pace.

Dean couldn’t get hard, not so soon, but he still moaned and pushed back desperately. God, it was so good. He needed this so bad, all the time. He was wrecked for everything but this. Castiel fucked through his brother’s cum, sending it dripping down Dean’s ass down to his balls, still nestled in the wet jockstrap.

“Fuck, Dean, so hot,” Castiel groaned. “Such a good boy for us. Knew you’d be a little slut. I would to fuck Jimmy senseless, telling him how I wished he was you. I’d fuck him in your bed, making him come all over your sheets.

“You’re always so fucking pretty, so needy. You walk around like you don’t even know how many people you get staring at your ass all day. You wear paper-thin jeans like you just have no idea that you look like a fucking whore. I’ve wanted you so bad for so long, and I didn’t even know you were really this slutty. I thought it was just wishful thinking, but you really are a little cockslut, aren’t you?”

Dean couldn’t fucking take it. He came again, dry, sobbing into the couch pillow where his face was buried. Castiel came too, rope after rope coating his insides just like his brother had before him. Fuck, it was almost too much.

Castiel caught his breath and pulled out. Jimmy was immediately there, a cup of ice water and a wet cloth in his hands. When had he gotten up? Dean gladly accepted the glass when it was held up to his mouth, drinking as much as he could before he needed to take a breath. One of the twins was cleaning him, peeling the jockstrap away and wiping his skin off.

They sat in silence for a bit, the twins watching Dean come back to earth. He eventually drank all the water and set the cup down. He then spoke. “So that happened.”

Jimmy chuckled nervously. “That, it did... Did you like it?”

“Yeah,” he said, feeling a little smile creep up his lips. “I did.”

“Good,” Castiel said, a matching smile gracing his own lips. “Because I know we both have a lot more planned for you.”

Dean looked between them, feeling almost giddy. The whole situation was still too crazy to not bother figuring out, but they would get to that eventually. For now, though? Dean just kissed Castiel’s cheek and curled into his chest. He grabbed Jimmy’s hand to intertwine their fingers, then spoke tiredly.

“I can’t wait.”

**Author's Note:**

> Let me know if you enjoyed this! I definitely have the lovely humanoids over on the Profound Bond Discord to thank for this. Those sprints actually got me on my ass and writing, and they totally encouraged me to follow my small boy heart into the depths of smut and depravity. ;)


End file.
